In the bowl of a stand mixer, whisk together ⅓ cup (80 grams) lukewarm water and yeast until dissolved. Add 1 cup (125 grams) flour; using the paddle attachment, beat at low speed until a stiff dough forms. (If flour is not incorporated, knead dough in bowl by hand until it is combined.) Cover and let rise in a warm, draft-free place (75°F/24°C) until doubled in size, 15 to 20 minutes.
Add 2 cups (250 grams) flour, granulated sugar, salt, and anise seed to yeast mixture. Add 2 eggs (100 grams), lukewarm milk, vanilla, and orange zest. Beat at low speed until a shaggy dough forms; scrape sides of bowl.
Switch to the dough hook attachment. Beat at low speed until dough is tacky, soft, smooth, and elastic, 6 to 8 minutes; add up to remaining ¼ cup (31 grams) flour, 1 tablespoon (8 grams) at a time, if dough is too sticky. Add butter, 1 tablespoon (14 grams) at a time, beating until combined after each addition (3 to 4 minutes total). Beat until a soft, smooth, and elastic dough forms, 5 to 7 minutes. Turn out dough onto a lightly floured surface, and shape into a smooth ball.
Lightly oil a large bowl. Place dough in bowl, turning to grease top. Cover and refrigerate overnight.
In a medium bowl, stir together raisins, candied orange, liqueur, cranberries, cherries, and remaining ⅓ cup (80 grams) lukewarm water. Cover and let stand overnight.
Lightly spray 2 (6-well) popover pans with baking spray with flour. Line wells with tulip-style paper baking cups. (See Note.)
Drain fruit mixture; pat dry with paper towels.
On a heavily floured surface, roll dough into a ½-inch-thick oval (about 12×10 inches). Sprinkle half of fruit mixture onto dough. Using a rolling pin, press fruit into dough. Fold dough in half lengthwise. Rotate dough 90 degrees. (Wipe off any liquid from fruit, and re-flour rolling pin if needed.) Roll dough into a ½-inch-thick oval. Sprinkle with remaining fruit. Press fruit into dough; fold dough in half lengthwise. Rotate dough 90 degrees, and roll into a ½-inch-thick oval. Divide dough into 12 portions (about 93 grams each). Using your hands, gently roll each portion into a smooth ball, lightly flouring your hands as needed. Place dough in prepared wells. Cover with lightly greased plastic wrap, and let rise in a warm, draft-free place (75°F/24°C) until doubled in size, about 1½ hours.
Preheat oven to 375°F (190°C).
In a small bowl, whisk remaining 1 egg (50 grams). Brush onto dough; sprinkle with pearl sugar.
Bake for 5 minutes. Reduce oven temperature to 350°F (180°C), and bake until golden brown and an instant-read thermometer inserted in center registers 190°F (88°C), 10 to 12 minutes more. Let cool in pans for 5 minutes. Remove from pans, and let cool completely on a wire racks. Store in an airtight container for up to 3 days.
